Wall Street To Y'all Street

Most founders dream of one nine-figure exit. She did it twice. And both times, the cost was higher than the check.

In this episode of Wall Street To Y'all Street, we sit down with a serial entrepreneur who built and sold two companies for over $100 million each — and hear the unfiltered truth about what those exits actually looked like behind the headlines. The deals that almost collapsed. The relationships that didn't survive. The identity crisis that hit harder the second time. And the lessons that only come from doing it twice.

This isn't a victory lap. It's a brutally honest conversation about what massive exits really do to the people who live through them — and what every founder needs to understand before they chase their own.

Whether you're building toward your first exit, already in negotiations, or just fascinated by what happens when founders cash nine-figure checks — this is the conversation nobody else is having.

🔑 In this episode:
• What two $100M+ exits actually looked like — beyond the press release
• The deal-killing moments that almost destroyed both sales
• Why the second exit was harder than the first (and not for the reason you'd think)
• The emotional and personal cost of building companies to sell
• What this founder would do differently if she could go back
• Hard-won lessons for any founder thinking about an exit

Find Deb Purvin on LinkedIn at https://www.linkedin.com/in/debpurvin/
Learn more about her company Business Owners MBA (BOMBA) at https://www.businessownersmba.com/

🎙️ABOUT THE HOST: Joseph J. Raetzer, MBA, JD is Corporate, Mergers & Acquisitions (M&A) and Securities Lawyer (capital raising). He started his career over 20 years ago on Wall Street and he has done over $100+ billion in transactions. He is also a serial entrepreneur with a successful 7-figure exit in under 3 years, and founder of his corporate M&A and securities law firm Raetzer PLLC.
His podcast Wall Street to Y’all Street features real lessons from founders, operators, and executives who have built, scaled, lost, and rebuilt businesses. This is not legal advice - always consult with your attorney. Joseph J. Raetzer, MBA, JD is licensed in New York and Texas. 🎙️
CONNECT WITH JOE ON LINKEDIN AT https://www.linkedin.com/in/raetzer/

Timestamps
00:00 Intro
03:20 Upbringing shaped a founder and operator
06:00 How did elite sports shape the way she thinks about business?
07:00 How does Deb keep founders focused and accountable?
08:20 How do you know when a “shiny object” is actually worth pursuing?
10:20 When does growth break a business’s backend operations?
12:00 What was the most expensive mistake Deb ever made as a founder?
13:00 How did she survive being $82 million in debt?
16:00 Could she have done anything to cushion that collapse?
18:00 Why building personal wealth alongside your business matters
19:10 Is debt dangerous or a critical tool for scaling?
20:00 What is the biggest mistake founders make with leverage?
21:20 Why you should never use debt to fund operating losses
23:00 What hidden liabilities can survive a bankruptcy purchase?
25:10 What is the biggest lie founders tell themselves about revenue?
26:00 Why Deb pushes founders to grow faster than they think
26:45 What are the three real ways to grow a business?
27:20 Why raising prices is one of the fastest ways to grow profit
28:20 What percentage of clients are usually not worth keeping?
29:20 Why founders price on cost instead of value
29:50 The townhouse story: how Deb left $1 million on the table
33:30 Why Deb focuses on founders in the “messy middle”
34:30 Why so many good business owners get stuck between $500K and $5M
35:20 What actually causes 82% of small businesses to fail?
36:20 The client story that shows how access to capital changes growth
38:10 Why cash flow fear holds founders back from scaling
39:20 Should founders grow fast and fix the numbers later?
42:20 Is a struggling business one quarter away from disaster?
43:00 Why failure usually happens slowly, not all at once
44:20 Why most accountants do not teach owners how to run a business
45:00 What numbers do big companies watch that small businesses ignore?
46:20 Is scaling from $2M to $10M harder than starting from zero?
48:20 What four things every business must get right to scale?
49:00 Why most founders who come to Deb are ready for help
50:00 What do banks actually look for when deciding to lend?
51:40 What makes a founder unlendable?
54:30 What is the number-one financial metric founders ignore?
55:20 Where does Deb start when fixing a business financially?
56:20 Why do so many smart entrepreneurs avoid their financial statements?
58:10 Why most business education ignores the numbers that matter
01:00:30 What keeps founders from asking for help?
01:02:10 How did Deb build a business that lets her live on a sailboat?
01:04:40 What does freedom actually look like when you scale correctly?
01:06:10 What would Deb say to the founder afraid to ask for help?